While the phanerogams or flowering plants annually contribute to the
list of newly discovered alkaloids, with the exception of muscarine
and amanitine, no alkaloid has as yet been definitely recognized among
the cryptogams.
Karl Bödeker, of Göttingen, has opened the road in this direction, and
gives in a paper sent to Liebig's _Annalen der Chemie_, August 15,
1881, the following account of an alkaloid, which, from the name of
the plant in which it occurs, he calls lycopodine.
The plant yielding the alkaloid, _Lycopodium complanatum_, belongs to
the group of angiospermous cryptogams. It is distributed throughout
the whole of north and middle Europe, and contains the largest
proportion of aluminum of any known plant. Its bitter taste led the
author to suspect an alkaloid in it.
To prepare the alkaloid the dried plant is chopped up and twice
exhausted with boiling alcohol of 90 per cent. The residue is squeezed
out while hot, and the extract, after being allowed to settle awhile,
is decanted off, and evaporated to a viscid consistency over a water
bath. This is then repeatedly kneaded up with fresh quantities of
lukewarm water until the washings cease to taste bitter, and to give a
reddish brown coloration when treated with a strong aqueous solution
of iodine. The several washings are collected and precipitated with
basic lead acetate, the precipitate filtered off, and the lead in the
filtrate removed by sulphureted hydrogen. The filtrate from the lead
sulphide is evaporated down over a water bath, then made strongly
alkaline with a solution of caustic soda, and repeatedly shaken up
with fresh quantities of ether so long as the washings taste bitter
and give a precipitate with iodine water. After distilling off the
ether, the residue is treated with strong hydrochloric acid, the
neutral or slightly acid solution filtered off from resinous
particles, slowly evaporated to crystallization, and the crystals
purified by repeated recrystallization. To prepare the pure base a
very concentrated solution of this pure hydrochlorate is treated with
an excess of a very concentrated solution of caustic soda, and pieces
of caustic potash are added, whereupon the free alkaloid separates out
at first as a colorless resinous stringy mass, which, however, upon
standing, turns crystalline, forming monoclinic crystals similar to
tartaric acid or glycocol. The crystals are rapidly washed with water,
and dried between soft blotting paper.
Thus prepared, lycopodine has a composition which may be represented
by the formula C_{32}H_{52}N_{2}O_{3}. It melts at 114° to 115° C.
without loss of weight. It is tolerable soluble in water and in ether,
and very soluble indeed in alcohol, chloroform, benzol, or amyl
alcohol. Lycopodine has a very pure bitter taste.
The author has formed several salts of the base, all of a crystalline
nature, and containing water of crystallization.
The hydrochlorate gives up a part of its water of crystallization at
the ordinary temperature under a desiccator over sulphuric acid, and
the whole of it upon heating.--_Chemist and Druggist._
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